CHEBI:27808 - heroin

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ChEBI Name heroin
ChEBI ID CHEBI:27808
Definition A morphinane alkaloid that is morphine bearing two acetyl substituents on the O-3 and O-6 positions. As with other opioids, heroin is used as both an analgesic and a recreational drug. Frequent and regular administration is associated with tolerance and physical dependence, which may develop into addiction. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:5680, CHEBI:24528
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Formula C21H23NO5
Net Charge 0
Average Mass 369.41100
Monoisotopic Mass 369.158
InChI InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1
InChIKey GVGLGOZIDCSQPN-PVHGPHFFSA-N
SMILES [H][C@]12C=C[C@H](OC(C)=O)[C@@H]3Oc4c(OC(C)=O)ccc5C[C@H]1N(C)CC[C@@]23c45
Roles Classification
Biological Role(s): opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing heroin (CHEBI:27808) has functional parent morphine (CHEBI:17303)
heroin (CHEBI:27808) has role μ-opioid receptor agonist (CHEBI:55322)
heroin (CHEBI:27808) has role opioid analgesic (CHEBI:35482)
heroin (CHEBI:27808) has role prodrug (CHEBI:50266)
heroin (CHEBI:27808) is a morphinane alkaloid (CHEBI:25418)
IUPAC Name
17-methyl-7,8-didehydro-4,5α-epoxymorphinan-3,6α-diyl diacetate
Synonyms Sources
(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol diacetate (ester) NIST Chemistry WebBook
3,6-Diacetylmorphine ChemIDplus
7,8-Dihydro-4,5-alpha-epoxy-17-methylmorphinan-3,6-alpha-diol diacetate ChemIDplus
Diacetylmorphine KEGG COMPOUND
Diacetylmorphine ChemIDplus
Diamorphine KEGG COMPOUND
Heroin KEGG COMPOUND
O,O'-Diacetylmorphine ChemIDplus
Database Links Databases
4412 DrugCentral
C06534 KEGG COMPOUND
D07286 KEGG DRUG
DB01452 DrugBank
Heroin Wikipedia
View more database links
Registry Numbers Types Sources
561-27-3 CAS Registry Number KEGG COMPOUND
561-27-3 CAS Registry Number ChemIDplus
561-27-3 CAS Registry Number NIST Chemistry WebBook
99261 Reaxys Registry Number Reaxys
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Last Modified
22 February 2017